Shelter Island Holidays from AU$808

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Your Shelter Island Holiday

From its highlights to its hidden delights, this city is best explored with a Shelter Island holiday package. Book a hotel in Orient Point, which is great for views, fishing and nature. If your trip to Shelter Island includes some sightseeing, don't miss popular attractions like 67 Steps Beach, Kontokosta Winery and Sag Harbour Marine Park. Check out Expedia's wide range of travel options and start organising your perfect holiday to Shelter Island now.

The Latest Shelter Island Holiday Deals

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
23 Aug - 25 Aug
found 6 hours ago
Return flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (2,108 reviews)
The rooms were large (for Manhattan) and the location was great for subways and trains out of Penn Station. Would definitely stay here again.

Reviewed on 17 Jun. 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
23 Aug - 25 Aug
found 6 hours ago
Return flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
Loved the eco friendly sustainable theme and abundance of plants in the foyer. Thoroughly enjoyed staying there - light crowd, quick check, pleasant staff. Room was on a smaller side but that is to be expected I guess given the location. Enjoyed staying in Dumbo with everything being walkable around us. Worth the money and experience. Wish the gym was bigger but we were the only ones that morning so didn’t bother us.

Reviewed on 15 Jun. 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
1 Sept - 8 Sept
found 3 hours ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9.2/10 Wonderful! (3,397 reviews)
The staff was very helpful with whatever questions we had. The room was clean, the buffet breakfast was good and the hotel’s location was excellent for our needs.

Reviewed on 22 Jun. 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
1 Sept - 8 Sept
found 3 hours ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9/10 Wonderful! (2,727 reviews)
2nd time at this property and will be back a third.

Reviewed on 23 Jun. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
1 Sept - 8 Sept
found 3 hours ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9.8/10 Exceptional! (1,205 reviews)
Best hotel I’ve ever stayed at ✌❤️

Reviewed on 19 Jun. 2025

Our guide on where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
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Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Shell Beach.

Find hotels in Menantic Creek

Shelter Island Holiday

Shelter Island Beach Holiday

There's nothing like a Shelter Island holiday to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Essential Information

Language
English
Currency
U.S dollars
Population
1,350
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Wolffer Estates Vineyard, East Hampton Main Beach and 67 Steps Beach

Our pick of the best Shelter Island Hotel Deals

Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,001 reviews)
"Gorgeous stay on a girls trip"

Reviewed on 21 Jun. 2025

Get rates
Montauk Yacht Club
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
The price is AU$155 per night from 29 June to 30 June
AU$155
29 June - 30 June
includes taxes & fees
7.6/10 Good! (978 reviews)
"Great location."

Reviewed on 19 Jun. 2025

Pier Blue Inn Old Saybrook - Essex
Montauk Blue Hotel
Montauk Blue Hotel
2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is AU$599 per night from 26 June to 27 June
AU$599
26 June - 27 June
includes taxes & fees
9.2/10 Wonderful! (78 reviews)
"Such a lovely stay. From the oceanfront views to every member working the hotel, one of the loveliest Montauk stays we’ve ever experienced."

Reviewed on 22 Jun. 2025

Montauk Blue Hotel
See all 4,739 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Shelter Island holiday package cost?
Offering excellent value package deals from AU$808 on Expedia, you'll be surprised at how little a holiday to Shelter Island costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Shelter Island?
To pick up cheap Shelter Island holiday packages, plan your trip outside of peak periods like public holidays and major festivals. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Shelter Island?
We recommend booking a Shelter Island holiday for at least 5 days. This will give you time to visit major attractions such as Menhadden Lane Beach and Havens House, and also check out neighbourhoods like Greenport West and The Heights. You might even be able to squeeze in a day trip outside of Shelter Island.
Is it worth booking a holiday package to Shelter Island?
It's easy to see why a Shelter Island holiday is on the to-do list of many travellers. Leading attractions like Shell Beach are just the start of things to keep you busy here.
How to find the best Shelter Island package deals?
Bagging a cheap Shelter Island package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable Shelter Island package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Shelter Island holiday as a package?
You can enjoy significant savings on your next Shelter Island getaway by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Shelter Island?
Land amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Shelter Island getaway.
How to plan a trip to Shelter Island?

  1. Pick your travel dates: What you'd like to do in Shelter Island and your favourite season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodation will likely be the largest expense during your trip to Shelter Island.
  3. Decide how many days away: Start by making a list of all the activities and sights you'd like to experience in Shelter Island. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your airfare and accommodation: After you've settled on your travel dates and duration, lock in the perfect Shelter Island holiday package for you.

Discover the most popular places to visit in Shelter Island

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Gardiner's Bay Country Club

Wades Beach

Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Wades Beach

What to do in Shelter Island

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

AU$245
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
See all activities in Shelter Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.